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Medicinal composition containing andrographolide derivatives and preparation method thereof and application

A technology of andrographolide and composition, which is applied in the field of pharmaceutical composition containing andrographolide derivatives and its preparation and application, which can solve the problems of undiscovered pharmacy research reports and achieve the effect of stable quality

Active Publication Date: 2008-10-15
SUZHOU LEINA PHARMA RES DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, the research group has synthesized hundreds of andrographolide derivatives, and screened them for anti-tumor, metabolism-regulating, and immune-regulating activities [PCT publication number: WO0185710], and obtained many valuable compounds, but found no In-depth pharmaceutical research report on this type of compound

Method used

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  • Medicinal composition containing andrographolide derivatives and preparation method thereof and application
  • Medicinal composition containing andrographolide derivatives and preparation method thereof and application
  • Medicinal composition containing andrographolide derivatives and preparation method thereof and application

Examples

Experimental program
Comparison scheme
Effect test

preparation example 13，1

[0036] Preparation Example 13, Preparation of 19-isopropylidene-14-acetylandrographolide (abbreviated as AP5)

[0037] Dissolve 5g of andrographolide (abbreviated as AP), 20mL of 2,2-dimethoxypropane and a catalytic amount of p-toluenesulfonic acid in 100mL of acetone, heat and reflux overnight, extract the reaction mixture with ethyl acetate, and the organic layer is sequentially washed with saturated NaHCO 3 Wash with saturated brine, anhydrous Na 2 SO 4 After drying, concentration, and silica gel column chromatography, 3,19-isopropylidene andrographolide (abbreviated as AP2) was obtained as a white solid. 1g AP2 dissolved in 10mL Ac 2 O, heated to reflux for 2 hours, the reaction mixture was extracted with ethyl acetate, the organic layer was successively water, saturated NaHCO 3 Wash with saturated brine, anhydrous Na 2 SO 4 dry. AP5 was obtained as a white solid by silica gel column chromatography. The molecular formula is: C 25 h 36 o 6 .

[0038]

[0039]...

preparation example 23，14

[0046] Preparation Example 23, 14, the preparation of 19-triacetylandrographolide (abbreviated as AP10)

[0047] 1g of andrographolide was dissolved in 10mL of Ac 2 O, heated to reflux for 2 hours, the reaction mixture was extracted with ethyl acetate, the organic layer was successively water, saturated NaHCO 3 and saturated brine, anhydrous MgSO 4 dry. AP10 was obtained as a white solid by silica gel column chromatography. The molecular formula is: C 26 h 36 o 8 .

[0048]

[0049] Compound confirmation data are as follows:

[0050] 3454, 3080, 2954, 1731, 1683, 1375, 1250, 1191, 1075, 1026, 895, 606.

[0051] 1 H (400MHz, CDCl 3 ):δ

[0052] 7.00 (td, J=6.84, 1.48Hz, 1H, H-12), 5.92 (d, J=5.96Hz, 1H, H-14), 4.90 (bs, 1H, H-17a), 4.60 (dd, J =11.68, 4.26Hz, 1H, H-15a), 4.55(dd, J=11.24, 6.08Hz, 1H, H-15b), 4.53(bs, 1H, H-17b), 4.36(d, J=11.80Hz , 1H, H-19a), 4.25(dd, J=11.24, 1.80Hz, 1H, H-3), 4.12(d, J=11.80Hz, 1H, H-19b), 2.52~2.37(m, 3H) , 2.12(s, 3H), 2...

preparation example 314，19

[0056] Preparation Example 314, the preparation of 19-diacetylandrographolide (AP12 for short) and 14-acetylandrographolide (AP13 for short)

[0057] 5g of andrographolide was added to 30mL of acetic acid, stirred and heated to 80°C, and reacted overnight. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with water and saturated brine successively, and anhydrous MgSO 4 dry. AP12 and AP13 were obtained by silica gel column chromatography. AP13 is a white solid. The molecular formula is: C 22 h 32 o 6 .

[0058]

[0059] Compound confirmation data are as follows:

[0060] 3436, 2927, 1738, 1641, 1384, 1233, 1077, 1024, 723, 621

[0061] 1 H (400MHz, Acetone): δ

[0062] 6.88 (td, J=6.92, 1.68Hz, 1H, H-12), 6.03 (d, J=6.04Hz, 1H, H-14), 4.87 (d, J=1.20Hz, 1H, H-17a), 4.59(d, J=1.08Hz, 1H, H-17b), 4.59~4.57(m, 1H, OH-19), 4.58(dd, J=10.94, 5.94Hz, 1H, H-15a), 4.26(dd , J=11.00, 1.76Hz, 1H, H-15b), 4.11 (d, J=10.88Hz, 1H, H-19a), ...

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Abstract

The invention relates to a pharmaceutical composition with andrographolide derivatives as active components, and a preparation method thereof. The andrographolide derivatives can be mixed with oil and emulsifying agent and made into emulsion for treating diseases due to excessive nitric oxide formation. The andrographolide derivatives have the following general formula, wherein R1 and R2 are selected from acetyl, hydroxy, alkyl, aryl, ceteroary, aralkyl, heteroaralkyl, alkyloyl group, alkenyloyl group, aroyl and heteroaroyl, or R1 and R2 are substituted by isopropylidene, and R3 is selected from Hydrogen or halogen.

Description

technical field [0001] The present invention relates to a pharmaceutical composition with the compound of the following general formula as an active ingredient and a preparation method thereof, specifically an emulsion and its preparation, and the application of the pharmaceutical composition in pharmacy. [0002] Background technique [0003] In 1896, Boorsma isolated a colorless crystalline substance from Andrographis paniculata for the first time. In 1911, it was identified as a diterpene lactone compound by Gorter structure, named androgrAPholide, and the Chinese name andrographolide, also known as Andrographolide B, is the compound of Andrographis paniculata. One of the main chemical components. Andrographolide has pharmacological activities such as anti-inflammatory, antipyretic, antiviral, antibacterial, immune regulation, inhibition of NF-κB, and antitumor. However, the structure of andrographolide determines that the chemical properties of andrographolide are re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/365A61K9/107A61K47/24A61K47/44A61P1/00A61P1/16A61P3/10A61P7/00A61P9/04A61P9/10A61P9/12A61P11/06A61P13/12A61P17/00A61P19/02A61P29/00A61P35/00A61P37/02
Inventor 滕厚雷赵烽邵萌关玉昆刘珂翟大伟
Owner SUZHOU LEINA PHARMA RES DEV
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